3,5-di-O-benzyl-2-deoxy-L-threo-pentono-1,4-lactone | 158976-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-di-O-benzyl-2-deoxy-L-threo-pentono-1,4-lactone
• 英文别名: 3O,5O-dibenzyl-2-deoxy-1,4-xylonolactone；(4S,5S)-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-2-one
• CAS: 158976-98-8
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: ZVNMIMFCDTZKSU-ROUUACIJSA-N

物化性质

• 沸点：
  474.0±40.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-di-O-benzyl-2-deoxy-L-threo-pentono-1,4-lactone 在 palladium dihydroxide 、 palladium on activated charcoal 吡啶 、 盐酸 、 ammonium hydroxide 、 lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 90.75h， 生成 (2R,3S)-2-(羟甲基)吡咯烷-3-醇盐酸
  参考文献：
  名称：

  A New Stereospecific Synthesis of 1,2,4-Trideoxy-1,4-Imino-D-Erythro-Pentitol

  摘要：

  1,2,4-Trideoxy-1,4-imino-D-erythro-pentitol [(2R,3S)-3-hydroxy-2-hydroxymethylpyrrolidine] (4) was synthesised from 2,5-di-O-tosyl-D-ribono-1,4-lactone in 42 % overall yield. The hey steps were deoxygenation at C-2 and a stereospecific inversion of the configuration at C-4. Compound 4 inhibited alpha-D-glucosidase (K-i = 25 mu M) and beta-D-glucosidase (K-i = 80 mu M).

  DOI：

  10.1080/07328300008544100
• 作为产物：
  描述：

  D-(+)-核糖酸-1,4-内酯 在 吡啶 、 氢氧化钾 、 三氟甲磺酸 、 溴 、 肼 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 生成 3,5-di-O-benzyl-2-deoxy-L-threo-pentono-1,4-lactone
  参考文献：
  名称：

  A New Stereospecific Synthesis of 1,2,4-Trideoxy-1,4-Imino-D-Erythro-Pentitol

  摘要：

  1,2,4-Trideoxy-1,4-imino-D-erythro-pentitol [(2R,3S)-3-hydroxy-2-hydroxymethylpyrrolidine] (4) was synthesised from 2,5-di-O-tosyl-D-ribono-1,4-lactone in 42 % overall yield. The hey steps were deoxygenation at C-2 and a stereospecific inversion of the configuration at C-4. Compound 4 inhibited alpha-D-glucosidase (K-i = 25 mu M) and beta-D-glucosidase (K-i = 80 mu M).

  DOI：

  10.1080/07328300008544100

文献信息

• Enantioselective Syntheses of 2-Deoxyxylono-1,4-lactone and 2-Deoxyribono-1,4-lactone from 1,3-Dioxan-5-yl Diazoacetates
  作者：Michael P. Doyle、Jason S. Tedrow、Alexey B. Dyatkin、Coenraad J. Spaans、Doina G. Ene

  DOI：10.1021/jo991211t

  日期：1999.11.1

  95% ee but with the mirror image configuration of that produced from the trans-2-(tert-butyl) analogue. The catalysts that are most suitable for these carbon-hydrogen insertion reactions are chiral dirhodium(II) carboxamidates. 1,3-Dialkoxy-2-propyl diazoacetates give mainly 2-deoxyxylono-1,4-lactone derivatives (>90:10) with generally high enantiocontrol, but replacement of hydrogen at the 2-position

  1,3-二恶烷-5-基重氮乙酸酯是用于高度非对映选择性和对映选择性碳氢插入反应的有价值的底物。反式-2-（叔丁基）-1,3-二恶烷-5-基重氮乙酸酯是2-脱氧核糖-1,4-内酯的直接前体，其ee含量高达81％，而顺式2-（叔丁基） ）-1,3-二氧杂-5-基重氮乙酸酯仅产生高达96％ee的受保护的2-deoxyxylono-1,4-lactone。但是，反式-2-芳基-1,3-二恶烷-5-基重氮乙酸酯（芳基=苯基或2-萘基）可形成2-deoxyxylono-1,4-lactone的前驱体，但可达95％ee，但带有镜反式-2-（叔丁基）类似物产生的图像构型。最适合于这些碳-氢插入反应的催化剂是手性氨基甲酸酯二氨基（II）。1,3-二烷氧基-2-丙基重氮乙酸酯主要产生2-deoxyxylono-1,4-lactone衍生物（> 90：
• Synthesis of 2-deoxyxylolactone from glycerol derivatives via highly enantioselective carbon-hydrogen insertion reactions
  作者：Michael P. Doyle、Alexey B. Dyatkin、Jason S. Tedrow

  DOI：10.1016/s0040-4039(00)76684-6

  日期：1994.6

  Diazodecomposition of 1,3-dialkoxy-2-propyl diazoacetates catalyzed by chiral dirhodium(II) carboxamides results in highly enantioselective and diastereoselective carbon-hydrogen insertion which forms 3,5-dialkyl 2-deoxyxylolactones in up to 98% enantiomeric excess.

  手性二吡啶（II）羧酰胺催化的1,3-二烷氧基-2-丙基重氮乙酸酯的重氮分解可导致高度对映选择性和非对映选择性的碳氢插入，从而形成3,5-二烷基2-脱氧二甲苯基内酯，其对映体过量高达98％。
• Chirality conversion method in lactone sugar compounds
  申请人：——

  公开号：US20020028955A1

  公开（公告）日：2002-03-07

  The present invention relates to a new process for effectively converting the chirality of 4- or 5-position carbon of a 1,4-lactone- or 1,5-lactone sugar compound which comprises reacting the lactone compound with secondary amine and sulfonyl group-containing compound. The compound of which chirality is converted according to the present invention can be advantageously used for preparing such expensive rare sugar compounds as L-ribose, D-talose, etc.

  本发明涉及一种有效转换 1,4-内酯或 1,5-内酯糖化合物 4 位或 5 位碳手性的新工艺，该工艺包括使内酯化合物与仲胺和含磺酰基化合物反应。根据本发明进行手性转换的化合物可以很好地用于制备 L-核糖、D-塔罗糖等昂贵的稀有糖类化合物。
• US6448415B1
  申请人：——

  公开号：US6448415B1

  公开（公告）日：2002-09-10
• A New Stereospecific Synthesis of 1,2,4-Trideoxy-1,4-Imino-D-<i>Erythro</i>-Pentitol
  作者：Birgitte Mølholm Malle、Inge Lundt、Richard H. Furneaux

  DOI：10.1080/07328300008544100

  日期：2000.1

  1,2,4-Trideoxy-1,4-imino-D-erythro-pentitol [(2R,3S)-3-hydroxy-2-hydroxymethylpyrrolidine] (4) was synthesised from 2,5-di-O-tosyl-D-ribono-1,4-lactone in 42 % overall yield. The hey steps were deoxygenation at C-2 and a stereospecific inversion of the configuration at C-4. Compound 4 inhibited alpha-D-glucosidase (K-i = 25 mu M) and beta-D-glucosidase (K-i = 80 mu M).